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Related Concept Videos

Cycloaddition Reactions: Overview01:16

Cycloaddition Reactions: Overview

Cycloadditions are one of the most valuable and effective synthesis routes to form cyclic compounds. These are concerted pericyclic reactions between two unsaturated compounds resulting in a cyclic product with two new σ bonds formed at the expense of π bonds. The [4 + 2] cycloaddition, known as the Diels–Alder reaction, is the most common. The other example is a [2 + 2] cycloaddition.
Cycloaddition Reactions: MO Requirements for Thermal Activation01:16

Cycloaddition Reactions: MO Requirements for Thermal Activation

Thermal cycloadditions are reactions where the source of activation energy needed to initiate the reaction is provided in the form of heat. A typical example of a thermally-allowed cycloaddition is the Diels–Alder reaction, which is a [4 + 2] cycloaddition. In contrast, a [2 + 2] cycloaddition is thermally forbidden.
Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids02:04

Oxidation of Alkenes: Anti Dihydroxylation with Peroxy Acids

Diols are compounds with two hydroxyl groups. In addition to syn dihydroxylation, diols can also be synthesized through the process of anti dihydroxylation. The process involves treating an alkene with a peroxycarboxylic acid to form an epoxide. Epoxides are highly strained three-membered rings with oxygen and two carbons occupying the corners of an equilateral triangle. This step is followed by ring-opening of the epoxide in the presence of an aqueous acid to give a trans diol.
Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide02:44

Oxidation of Alkenes: Syn Dihydroxylation with Osmium Tetraoxide

Alkenes are converted to 1,2-diols or glycols through a process called dihydroxylation. It involves the addition of two hydroxyl groups across the double bond with two different stereochemical approaches, namely anti and syn. Dihydroxylation using osmium tetroxide progresses with syn stereochemistry.
Radical Autoxidation01:20

Radical Autoxidation

The oxidation of an organic compound in the presence of air or oxygen is called autoxidation. For example, cumene reacts with oxygen to form hydroperoxide. Autoxidation involves initiation, propagation, and termination steps. Many organic compounds are susceptible to autoxidation—especially ethers in the presence of oxygen, which form hydroperoxides. Even though this reaction is slow, old ether bottles contain small amounts of peroxide, which leads to laboratory explosions during ether...
Oxidation of Phenols to Quinones01:17

Oxidation of Phenols to Quinones

In the presence of oxidizing agents, phenols are oxidized to quinones. Quinones can be easily reduced back to phenols using mild reducing agents. The electron-donating hydroxyl group enhances the reactivity of the aromatic ring, enabling oxidation of the ring even in the absence of an α hydrogen.
o-hydroxy phenols are oxidized to o-quinones and p-hydroxy phenols to p-quinones. Such redox reactions involve the transfer of two electrons and two protons. The reversible redox property is crucial in...

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Formation of Covalent DNA Adducts by Enzymatically Activated Carcinogens and Drugs In Vitro and Their Determination by 32P-postlabeling
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Formation of Covalent DNA Adducts by Enzymatically Activated Carcinogens and Drugs In Vitro and Their Determination by 32P-postlabeling

Published on: March 20, 2018

Co-oxidation by cyclooxygenases.

Lawrence M Szewczuk1, Trevor M Penning

  • 1GlaxoSmithKline, Collegeville, Pennsylvania, USA.

Current Protocols in Toxicology
|October 10, 2012
PubMed
Summary
This summary is machine-generated.

Cyclooxygenases (COXs) use a heme cofactor for prostaglandin synthesis. This study characterizes the co-oxidation side reaction essential for COX enzyme function and prostaglandin production.

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Formation of Covalent DNA Adducts by Enzymatically Activated Carcinogens and Drugs In Vitro and Their Determination by 32P-postlabeling
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Area of Science:

  • Biochemistry
  • Enzymology

Background:

  • Cyclooxygenases (COXs) synthesize prostaglandins (PGs) from arachidonic acid (AA).
  • COX enzymes utilize a heme cofactor for peroxide bond cleavage, involving iron oxidation states Fe(3+) to Fe(5+).
  • Catalysis requires electron transfer from co-reductants to regenerate the resting Fe(3+) state via co-oxidation.

Purpose of the Study:

  • To characterize the co-oxidation side reaction in cyclooxygenases (COXs).
  • To understand the role of co-reductants in COX enzyme catalysis.

Main Methods:

  • Enzyme assays to monitor COX activity.
  • Spectroscopic methods to analyze heme redox states.
  • Characterization of co-reductant interactions with COX enzymes.

Main Results:

  • Demonstrated the occurrence of compound I and II intermediates during COX catalysis.
  • Identified key co-reductants involved in the COX catalytic cycle.
  • Quantified the contribution of co-oxidation to overall COX activity.

Conclusions:

  • Co-oxidation is a critical side reaction for cyclooxygenase (COX) function.
  • Understanding co-oxidation is essential for comprehending prostaglandin synthesis.
  • This research provides protocols for studying COX co-oxidation.